N-substituted fatty acid amide lubricants

ABSTRACT

This invention relates to N-acylmorpholines and N-mono and N,Ndisubstituted fatty acid amides and to similar derivatives of epithioamides which are useful as base and extreme pressure lubricants and additives.

United States Patent Magne et a1.

[11] 3,849,321 [451 Nov. 19, 1974 N-SUBSTITUTED FATTY ACID AMIDE LUBRICANTS Inventors: Frank C. Magne, 2223 Franklin Ave., New Orleans, La. 701 17; Robert R. Mod, 4600 San Marco Rd., New Orleans, La. 70129; Gene Sumrell, 134 Wren St., New Orleans, La. 70124; Winfred E. Parker, 420 W. Upsal, Philadelphia, Pa. 19119 Filed: Apr. 6, 1973 Appl. No.: 348,801

Related US. Application Data Division of Ser. No. 176,734, Aug. 31, 1971, Pat. No. 3,746,644.

US. Cl 252/46.7, 252/463, 252/499, 252/515 A Int. Cl. Cl0m l/46, ClOm H48 58 Field of Search 252/467, 49.9

Primary Examiner-H. Sneed Attorney, Agent, or Firm-M. Howard Silverstein; Max D. Hensley [57] ABSTRACT This invention relates to N-acylmorpholines and N- mono and N,N-disubstituted fatty acid amides and to similarderivatives of epithioamides which are useful as base and extreme pressure lubricants and additives.

2 Claims, N0 Drawings I N-SUBSTITUTED FATTY ACID AMIDE LUBRICANTS This is a division, of application Ser. No. 176,734 filed Aug. 31, 1971 now U.S. Pat. No. 3,746,644.

A non-exclusive, irrevocable, royalty-free license in the invention herein described, throughout the world for all purposes of the United States Government, with the power to grant sublicenses for such purposes, is hereby granted to the Government of the United States of America.

This invention relates to certain compounds which are N-fatty acyl derivatives of primary and secondary amine and N-substituted acyl derivatives of primary and secondary amines which have exhibited utility as base lubricants, extreme pressure lubricants or lube additives. More particularly, this invention relates to N- and NN-disubstituted long chain aliphatic amides the acyl component of which is a normal, branched, or substituted alkenoic or alkanoic acyl group containing from 16 to 22 carbon atoms the amide nitrogen of which may be derived from an alkyl amine, dialkyl amine, alkylalkoxyalkylamine, dialkoxyalkylamine or nitrogen heteroalicylic Typical amines are butylamines, dibutylamines, N-methyl-alkoxyethyl V amine, dieth'oxyethyl amine, and morpholineThe acyl substituent referred to may be divalent sulfur or pentavalent phosphorus.

We have discovered that many of the simple N-alkyl and N,N-dialkyl or N-alkyl-N -alkoxyalkyl amides of the C to C alkeneoic or alkanoic fatty acids are good base lubricants. We have further discovered that the introduction of divalent sulfur into the fatty acid moiety imparts excellent extreme pressure lubricant characteristics to such compounds. In particular we have found the epithio group to be most effectiveTW e have also observed that the introduction of both hydroxy and alkyl phosphato groupings alpha to each other also imparts extreme pressure lubricant characteristics to the compound.

In addition it was noted that the above hydroxy phosphato compound and its mercapto analog N- [9( l)-mercapto-( 9) l O-dibutylphosphato]stearamide were effective antiwear compounds and additives.

lncluded among the specific compounds operable as base lubricants are N-methyl-N-butyloleamide, N-ethoxyethoxyethoxy propyloleamide, N- ethoxyethoxy propyloleamide, N-

methoxyisopropyloleamide, N-methoxyethyloleamide. Compounds showing particular promise as extreme pressure lubricants or additives are N,N-dibutyl-9,10- epithiostearamide, N,N-dibutyl-9, -12, 1 3-diepithiostearamide, 9,10-epithiostearoyl morpholine, N- ethoxyethoxyethoxypropyl-9, l O-epithiostearamide, N- 9, l0-12,1 3-diepithiostearoylmorpholine and N-[9( 10)- hydroxy-9( 10)-dibutylphosphato]stearamide.

Compounds showing particular promise as antiwear additives are N,N-dibutyl-[9( l0 )-hydroxy-( 9) l 0- dibutylphosphato]stearamide and N,N- [9( l0)mercapto-(9) lO-dibutylphosphatostearoyl]morpholine.

Example 1 N-Methyl-N-butyloleamide grams (0.33 mole) of oleoyl chloride was added dropwise and with stirring to a mixture of 29 grams (0.33 mole) of N-methyl-N-butylamine and 27 grams (0.33 mole) of pyridine. Stirring was continued until the heat of reaction subsided. The solid pyridine hydrochloride was filtered off and the filtrate was washed successively with aqueous HCl and water until acid free. It was dried stripped, percolated through an activated alumina column, and the product removed from the percolate by stripping off the solvent. Analysis of the product: Percent C, 78.87 (theory 78.63; percent H, 13.02 (theory 12.82); percent N, 3.96 (theory 3.99).

Example 2 N,N-dibutyloleamide This material was prepared by the procedure of Example 1 from 100 grams (0.33 mole) of oleoyl chloride 42.5 grams (0.33 moles of di-n-butylamine and 27 grams (0.33 mole) pyridine. Analysis of the product: Percent C, 78.94 (theory 79.25); percent H, 13.16 (theory 13.06); percent N, 3.44 (theory 3.56) confirm thepreparation.

Example 3 Example 4 Ethoxyethoxypropyloleamide This material was prepared by the procedure of Example 1 from 100 grams (0.33 mole) of oleoyl chloride, 58.3 grams (0.33 mole) ethoxyethoxypropylamine and 27.0 grams (0.33 mole) of pyridine. Analyses of percent C, 71.45 (theory 73.80); percent H, 11.87

' (theory 12.07); and percent N, 2.92 (theory 3.18) confirm the preparation.

Example 5 Methoxyisopropyloleamide This material was prepared by the procedure of Example 1 from 100 grams (0.33 mole) of oleoyl chloride, 29.3 grams (0.33 mole) methoxyisopropylamine and 27.0 grams (0.33 mole) pyridine. Analysis of percent C, 73.15 (theory 74.99); percent H, 12.01 (theory 1 1.93); and percent N, 3.67 (theory 3.97) confirm the preparation.

Example 6 Methoxyethyloleamide This material was prepared by the procedure of Example 1 from 100 grams (0.33 mole) of oleoyl chloride, 24.4 grams (0.33 mole) of methoxyethylamine and 27.0 grams (0.33 mole) pyridine. Analysis of percent C, 73.08 (theory 74.55); percent H, l 1.98 (theory 11.83); and percent N, 3.31 (theory 4.14) confirm the preparation.

Example 7 Oleoylmorpholine This material was prepared by the procedure of Example 1 from 100 grams (0.33 mole) of oleoyl chloride, 28.7 grams (0.33 mole) of morpholine and 27.0 grams (0.33 mole) of pyridine.

Example 8 N,N-dibutyllinoleamide This product was prepared following the exact procedure of Example 2 except for the substitution of oleoyl chloride by linoleoyl chloride.

Example 9 N,N-dibutyl-9, l O-epithiostearamide 120 grams (0.30 mole) of N,N-dibutyloleamide was epoxidized by the addition with stirring of 62.0 grams (0.36 mole) of meta-chloroperbenzoic acid in 630 ml of chloroform. Reaction was continued for 1 hour beyond final addition and the excess peracid destroyed by a small amount of a solution of Na SO The metachlorobenzoic acid was removed by a Nal-lCO wash, followed by water washing. The Cl-lCl solutionwas then dried with anhydrous Na SO and the CHCI stripped off to recover the product N,N-dibutyl-9,10- epoxystearamide, oxirane content 3.45% (theory 3.91%). 100 grams (0.24 mole) of this product was added to a well stirred slurry of 55.7 g (0.75 moles) of thiourea and 89.5 g (0.72 moles) of benzoic acid in acetone. Stirring was continued for 3 hours beyond the terminal addition whereupon the benzoic acid was washed out with 38.8 g (0.36 mole) of Na CO and the organic product extracted with hexane. The organic phase extract was dried and stripped to recover the product N,N-dibutyl-9,IO-epithiostearamide containing 6.41% sulfur (theory 6.67%).

Example 10 N-( 9, IO-epithiostearoyl )morpholine This product was prepared by the exact procedure described in Example 9 except for the substitution of oleoylmorpholine for the N,N-dibutyloleamide of Example 9. Analysis of product showed percent C, 71.22 (theory 69.34); percent H, 11.22 (theory 10.77); percent N, 3.66 (theory 3.68); percent S, 3.44 (theory 7.80).

Example 1 l N,N-dibutyl-9, 10-1 2, 1 3-diepithiostearamide 10.76);

This product was prepared following the procedure described in Example 9 except for the replacement of the N,N-dibutyloleamide of Example 9 by N,N- dibutyllinoleamide, and a doubling of the molar ratios of all reagents. The product analyzed as follows: percent C, 69.64 (theory 68.57); percent H, 10.93 (theory 10.76; percent N, 3.10 (theory 3.07); percent S, 11.7 (theory 14.06).

Example 12 N-Ethoxyethoxyethoxypropyl-9,10-epithiostearamide To 166 g of N-ethoxyethoxyethoxypropyl oleamide, Example 3, was added dropwise and with stirring 73.8 g of m-chloroperbenzoic acid in 800 ml of CHC1 The spent m-chloroperbenzoic acid was removed with 10% aqueous NaHCO and the epoxide recovered by drying and stripping off the CHCl 171 g of this epoxide was added dropwise to a slurry of 56 g thiourea in 1,000 ml of acetone and the concurrent addition of 43.4 g of glacial acetic acid and the reaction mixture stirred for 3 hours. The glacial acetic acid was neutralized with Na CO and the episulfide, N-ethoxyethoxyethoxypropyl- 9,10-epithiostearamide, extracted with Skellysolve B and washed, dried, and stripped. Its elemental analysis was C 67.1 (66.52), H 11.42 (10.88), N 2.67 (2.87), S 2.29 (6.57).

Example 1 3 N-Ethoxyethoxyethoxypropyl-9( 10)mercaptostearamide 173 g of N-ethoxyethoxyethoxypropyloleamide in CCL, was treated in the cold with a CCL, solution containing 60.9 g of bromine. Any unreacted bromine was removed by a thiosulfate wash. 140 g of the resulting dibromo compound was added dropwise to a well stirred solution of 72 g of Na S.9l-l O in dimethylsulfoxide maintained at C. Stirring was continued at 80C for 3 hours. Water was added and the reaction product was extracted with hexane; washed, dried, and stripped. Elemental analysis of the product was C 66.3 (66.5); 1-1 11.1 (10.9), N 2.7 (2.9), S 4.4 (6.8).

Example 14 N,N-Dibutyl-9( 10)[dibutylphosphono]stearamide g of N,N-dibutyloleamide, Example 2, 148 g of dibutyl phosphite, and 1.29 of benzoyl peroxide catalyst were heated at C for 3% hours. Additional units of 1.29 g of benzoyl peroxide was added after the first and second hours of reaction time. The excess dibutyl phosphite was then removed by distillation at reduced pressure, 0.45 mml-lg. The stillpot contents showed strong adsorption bonds at 8, 9.3, and 9.7 microns characteristics of the phosphonate group. The elemental analysis was C obs 71.46 (69.50), H obs 12.42 (11.92), N obs 2.20 (2.38), P obs 4.24 (5.28) percent respectively.

Example 15 N-9,l0-12,13-diepithiostearoylmorpholine This product was prepared by the same procedure described in Example 9 except for the substitution of linoleoyl morpholine for the N,N-dibutyloleamide of Example 8 and the doubling of molar proportions of the rn-chloroperbenzoic acid in the epoxidation step and the thiourea and benzoic acid in the epithioation step. The elemental analysis was C obs 68.83 (63.92), H =obs 10.26 (9.44), N =obs 3.29 (3.38), S obs 4.00 (15.49) percent respectively.

Example 16 N,N-Dibutyl-[9( l0)-hydroxy-( 9) 1 O-dibutylphos- I phato]stearamide 44.7 g of dibutylhydrogen phosphate was added to 182.2 g of N,N-dibuty1-9,l0-epoxystearamide at 90-95C with stirring. Reaction conditions were continued for 3- /2 hours after termination of the addition. The reaction product was dissolved in commercial hex ane and the unreacted dibutyl hydrogen phosphate neutralized and washed out with portions of aqueous 10 NaHCO followed by several water washes. Acidulation of the hexane phase with diluted l-lCl followed by several water washes, drying and stripping, yielded the product. Elemental analysis was, C obs 66.56 (65.91 H obs 11.04 (11.30), N =obs 2.90 (2.26), P obs 3.04 (4.20).

5 Example 17 N-[9( 10)mercapto-( 9 1 O-dibutylphosphatostearoyl]morpholine 12 g of dibutylhydrogen phosphate was added'dropwise with stirring to 51.0 g of (9,10-epithiostearoyl)- morpholine, the preparation of Example 10, at 8590C and the heating and stirring continued for 3 hours beyond the terminal addition. The reaction product was dissolved in commercial hexane and any excess or unreacted ii Earwas neutralized and washed out with aqueous 10% NaHCO The hexane extract was washed several times with water dried and stripped. The elemental analysis of the product was C obs 66.74 (69.36), H =obs 10.69 (11.05), N obs 2.89 (3.32), S obs 3.27 (2.17), P obs 1.68 (2.10) percent respectively.

Example 1 8 TABLE I ANTIWEAR LUBRICANT PROPERTIES OF FATTY ACID AMlDES COMPOUND without with 5% additive additive Additive 1. N,N-Bis(2-ethoxy- N,N-Di-buty1-9.l0-epi- Y ethyl)o1eamide 0.597 0.735 thiostearamide 2. N.N-Di-n-butyl-9,l0- I epithiostearamide 0.842 none 3. Oleoylmorpholine 0.623 0658 do. 4. N,N'dimethylo1eamide 0.797 0.987 do. 5. N.N-Di-n-propylo1eamide 0.908 0.885 do. 6. N,N-Di-n-hexyloleamide 0.893 0.898 do. 7. N.N-Di-n-butylerucamide 0.758 0.798 do. 8. N,N-Di-n-butyl amide of Se]. hydrogenated cottonseed fatty acids 0.798 0.958 do. 9. N.NBis(2-Methoxyethyl)oleamide 0.626 0.725 do. 10. N,N-dibuty1o1eamide 0.710 ll, N-Oleoyl-4-propy1- piperidine 0.847 12. Morpholide of sel.

hydrogenated cottonseed fatty acids 0.642 l3. N-Methyl'N-butyloleamide 0.607 14. N-Ethoxyethoxyethoxypropyloleamide 0.503 15. N-Ethoxyethoxypropyloleamide 0.526 l6. N-Methoxyisopropyloleamide 0.705 17. N-Methoxyethyloleamide 0.420 18. 102 sec Paraffin Oil 0.902 N-Methoxyethylole amide 19. 0.0.8. 0.906 do. 20. N.N-Dibutyl-9(l0)' carbobutoxyoctadecanamide 0.610 21. 102 sec Paraffin Oil 0.818 N,N-Dibutyl-9( l0)- carbobutoxyoctadecanamide 22. D05. 0.945 do. 23. N-[9(l0)mercapto- (9)10-dibuty1- phosphatostearoyll 0.615 morpholine 24. 102 sec Paraffin Oil 0.552 N-[9( l0)mercapto- (9)10-dibuty1phosphatostearoyllmorpholine 25. D.O.S. 0535 do. 26. N,N-Dibuty1-[9(l0)- hydroxy(9)10-dibutylphosphatol stearamide 0.498 27. 102 sec Paraffin Oil 0.498 N.N-Dibutyl-[9( l0)- hydroxy-( 9 l O-dibutylphosphatol stearamide ANTlWEAR LUBRICANT PROPERTIES OF FATTY ACID AMIDES Avg. Wear Scar, mm

COMPOUND without with 5% additive additive Additive I 28. o.o.sv 0.49s

29. N,N-Dibutyl-9(l0)- [dibutylphosphono] stearamide 0.530 30. N-Ethoxyethoxyethoxypropyl-9.lepithiostearamide 0.707 3l. N-EthoxyethoxyethoxypropyL)! llllmcrcapto- .iuarumidc 0.690 32 N-ILH)l2,l3-dicpithin zlmunyl)Inurplmlmz: 0.065 33. HistZ-cthylhexylJseba cale 0.872 34. 100 sec Paraffin Oil 0.803 35. Aero Shell (Mil- 7808) 0.587 36. Gulf Pride. Single G, MS, multiviscosity 0.447 37. I00 sec Puraffin Oil 0.813 N.N-Dibutyl-9.l0- l2, l3-Diepithiostearamide 38. Bis(2 ethylhexyl) sebacate 0.836 do. 39. I00 sec Paraffin Oil 0.723 N-9,lO-epithiosteuroyl morholine 40. Bis(2 ethy|hexyl) sebacate 0.9l5 do. 4Iv I00 sec Paraffin Oil 0.917 N,N-Dibutyl-9.l0-

dichlorostearamide 42. Bis(2-ethylhexyl) sebucate 0.848 do.

It can be seen from the data presented that the N- Example 19 alkoxyalkyl and N,N-di(alkoxyalkyl)oleamides, without the assistance of additives, exhibited wear characteristics (i.e., low scar diameters) comparable to the The various mides were evaluated as extreme prescommercial controls Aeroshell and Gulfpride, which sure lubricants or additives in a Shell 4-ball extreme do contain additives to improve performance. N,N- pressure tester at 1,440 RPM following ASTM Procedibutyl-[9( l0)'hydroxy-(9)l0-dibutylphosphato1- dur'e D 2596-67T. Loads were increased in increments stearamide and N-[9( l0)mercapto-(9)l0- of 20 Kg to weld point and the test run for one minute dibutylphosphatostearoyl]morpholine not only exhibit 40 or to weld whichever occured first. Commercial hypoid low wear characteristics in themselves but also impart fluid SAE No. was employed as the control E.P. luas additives such characteristics to paraffin oil and bricant. The performance of the amides tested is given DOS base lubricants. in Tables II, III, and IV.

' TABLE II EXTREME PRESSURE TESTS (ASTM D2596-67T) Weld Point Weld Point 20. SAE No. 90 Commercial hypoid fluid 280 TABLE 111 EVALUTATION OF N.N-DIBUTYL-9,I-12.I3-DI-EPITHIOSTEAR- AMIDE AS AN ADDITIVE AND AS A BASE OIL IN EXTREME PRESSURE TESTS. (ASTM D2596-67T) BASE OIL "/1 ADDITIVE LOAD, Kg WEAR SCAR HIM/c1. Iuruffln Oil (57/ 14! 1 90 '1',- liu 2 r10 r11, 22 (In (In 24 Weldsec.

Bis( 2-ethylhexy1)sebacate (5%) 120 1.51 do. do. 180 1.59 do do. 1901 LS. )hu al 2.47 do. do. 200 Weld-4 sec. do. 240 2.88 do. do. 260 3.5 do do. 270 We1d10 sec.

N,N-DibutyI-9,10-12.13-

diepithiostearamide None 1.38 do. do. 160 1.61 do. do. 200 1.89 do. do. 280 2.13 do. do. 320 2.47 do. do. 360 2.70 do. do. 400 2.88 do. do. 440 WeId-46 sec "'Incipienl seizure EXTREME PRESSURE TESTS ON N-EXTHOXYETHYOXYETHOXYPROPYL-J,IO-EPI- THIOSTEARAMIDE (PC-O-No. 7682) BASE OIL ADDITIVE APPLIED LOAD AVE. SCAR 7682 None 120 1.05

do. do. 160 1.75 do. do. 240 2.35 do. do. 300 2.19 do. do. 340 2.55 do. do. 360 I 2.62 do. do. 380 weld 102 sec Paraffin 011 7682 (5%) 120 2.28 do. do. 2.46 do. y do. weld o.o.s. 7682 (5%) 120 2.23 do. do 140 2.44

do. do: 150 weld EXTREME PRESSURE TESTS ON N-ETHOXYETHOXYETHOXYPROPYL-9( 10)- MERCAPTOSTEARAMIDE (PC-O-No. 7683) BASE 01L ADDITIVE- APPLIED LOAD AVE. SCAR Kq mm 7683 None 200 1.54 do. do. 300 2.26 do. do. 400 2.25 do. do. 450 2.15

do. do. 500 2.15"

102 sec Paraffin OiI 7683 (5%) 120 1.97 do. do. 140 2.35 do. do. 150 2.54 do. do. weld D.O.S. 7683 (5'71) 120 1.68 do. do. 140 2.18 do. do. 160 2.59 do. do. 2.72 do. do. weld "Test stopped boc usc of exlremo dccomposit ion. not weld.

EXTREME PRESSURE TESTS ON N'(9,I0-I2,I3-DIEPITHIOSTEAROYL)MORPHOLINE (PC-O-No. 7684) BASE 01L ADDITIVE APPLIED LOAD AVG. SCAR Kq mm v 7684 None 200 2.21 do. do. 90 2.18 do. do. 100 2.45. do. do. 121) weld Test stopped because of 2111; decomposition and noxious fumes. Did not wold.

TAB LE III Continued EXTREME PRESSURE TESTS ON N-(LIO- I 2,I 3-DIEPITHIOSTEAROYL)MORPHOLINE IPC-U-No. 7684) BASF. OII. ADDITIVE. APPLIED LOAD AVG. SCAR Kq mm do. do. 260 2.38 do. do. 340 2.43 do. do. 400 2.75 do. do. 460 2.90 do. do. 500 2.98"

102 sec Paraffin OiI 7684'(5%) 100 2.23 do. do. 120 2.61 do. do. 130 2.74 do. do. 140 weld D.O.S. 7684 (5%) 120 2.54 do. do. I40 2.58 do. do. I50 weld N-Methoxyethyl oIeamide 7684 (5%) I40 2.53 do. do. I60 2.77 do. do. I70 weld "Test stopped because of extreme decomposition. Did not weld.

EXTREME PRESSURE TESTS ON N,N-DIBUTYL-9( I)-(DIBUTYLPHOSPHONO)STEARAMIDE (PC-O-No. 7685) APPLIED LOAD AVE. SCAR. BASE OIL ADDITIVE Kg mm 7685 None 120 3.05 do. do. I40 4.50 do. do. I50 weld EXTREME PRESSURE TESTS ON N.N-DIBUTYL-[9( IO)-HYDROXY-9( I0)- DIBUTYLPHOSPHATOlSTEARAMIDE (POO-No. 7686) 7686 None 200 0.887 do. do. 300 2.78 do. do. 340 4.32 do. do. 350 4.50 do. do. 360 weld I00 sec Paraffin Oil 7686 I 2.28 do. do. I40 280 do. do. I 3.0I do. do. I weld D.O.S. 7686 (5%) I20 L95 do. do. I40 2.85 do. do. I50 3.03

do. do. 160 weld M EXTREME PRESSURE TESTS ON N-[9( I0)-MERCAPTO-9( I0)-DIBUTYLPHOSPHATOSTEAROYLIMORPHOLINE (OC-O-No. 7687) APPLIED LOAD AVE. SCAR. BASE OIL ADDITIVE Kg mm 7687 None I20 0.608

do. do. 160 1.45 do. do. 200 1.40 do. do. 240 1.70 do. y do. 280 3.36"

EXTREME PRESSURE TESTS ON N,N-DIBUT YL-(I0)- CARBOBUTYOXYOCTA-DECANAMIDE (PC-O-No. 7688) 7688 None 1.92 do. do. 2.18 do. do. I00 2.45 do. do. I20 weld Test stopped because of extreme decomposition and noxious fumes. Did not weld.

TABLE IV EVALUATION OF N-QJO-EPIOTHIOSTEAROYL MORPHOLINE AS AN ADDITIVE AND AS A BASE OIL IN EXTREME PRESSURE TESTS (ASTM D 2596-67T) LOAD WEAR SCAR BASE OIL ADDITIVE Kg min sec Paraffin Oil (5%) 2.00 do. do. I40 2.80 do. do. I60 3.25

do. do. I80 weld. I0 sec.

TABLE IV- 7 Continued EVALUATION OF N-9,l EPlOTHlOSTEAROYL MORPHOLlNE AS AN ADDlTlVE AND AS A BASE OlL IN EXTREME PRESSURE TESTS (ASTM D 2596-67T) We claim:

1. A composition of matter useful as a lubricant and having antiwear and extreme pressure lubricating properties, said composition comprising paraffin oil and to weight percent of N,N-dibutyl-[9( l0)-hydroxy- (9) 1 O-dibutylphosphatolstearamide.

2. A composition of matter useful as a lubricant and having antiwear and extreme pressure lubricating properties, said composition comprising paraffin oil and 5 to 10 weight percent of N-[9( l0)-mercapto-(9)l0- dibutylphosphatostearoyl]morpholine.

UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION PATENT NO. 3,849,321

DATED I November 19, 1974 INVENT R( I Frank C. Magne, Robert R. Mod, Gene Sumrell 8:

Winfred E. Parker It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:

The following statement should appear in the heading in col 1:

Assignee: The United States of America, as

represented by the Secretary of Agriculture.

Signed and Scaled this twenty-eight Day Of October 1975 [SEAL] Arrest.

RUTH C. MASON c. MARSHALL DANN Arresting 01ft?? Commissioner uj'PaIents and Trademarks 

1. A COMPOSITION OF MATTER USEFUL AS A LUBRICANT AND HAVING ANTIWEAR AND EXTREME PRESSURE LUBRICATING PROPERTIES, SAID COMPOSITION COMPRISING PARAFFIN OIL AND 5 TO 10 WEIGHT PERCENT OF N,N-DIBUTYL-(9(10)-HYDROXY-(9)10DIBUTYLPHOSPHATO)STEARAMIDE.
 2. A composition of matter useful as a lubricant and having antiwear and extreme pressure lubricating properties, said composition comprising paraffin oil and 5 to 10 weight percent of N-(9(10)-mercapto-(9)10-dibutylphosphatostearoyl) morpholine. 